What a Kawhi Leonard Extension Looks Like for Raptors

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Now that the Toronto Raptors have traded for Kawhi Leonard, they have a chance to sign him to a long-term deal that will allow him to finish his career in Canada.
Leonard has one year remaining on his contract that will pay him just north of $50 million, and is eligible to sign a two-year deal, which is expected to be signed before the start of the regular season.
"Safe bet: The wait for Leonard's expected two-year extension with the Raptors will be a lot shorter than what Toronto and its fans just endured to bring the 2019 NBA Finals MVP back to Canada," NBA insider Jake Fischer wrote.
Kawhi Leonard Signing an Extension Soon

When Leonard arrived in Toronto in 2018, there was an understanding that he would only be there for one year, and the Raptors had to take advantage of the opportunity that season. Toronto did just that and won their first and only NBA championship to date, but Leonard's second stint with the franchise is expected to be a little bit longer.
Leonard turned 35 years old this offseason and is hoping to finish out his Hall of Fame career with the Raptors. A two-year extension would get him to the end of the 2028-29 campaign, just before his 38th birthday. By then, the Raptors will know whether or not they have a potential winning formula, giving them enough time to work things out.
Is an Extension Too Much?

The Raptors traded a pretty big haul for Leonard, parting ways with All-Star forward Brandon Ingram, fourth-year shooting guard Gradey Dick, two first-round picks, two second-round picks, and a pick swap. That's far more than what the Raptors gave up for Leonard back in 2018, when he was with the San Antonio Spurs. It would be a disservice to the Raptors if they did not get an extension done with Leonard before the start of the season.
The Raptors are pushing their chips in and going all in on building a roster around Leonard and Scottie Barnes. This is the necessary risk that needs to be taken in order to win a championship, and the Raptors are ready to push forward with this core.
The Raptors might be limiting themselves for the future, but they have to commit to Leonard in order to try and win it all.
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Jeremy Brener is the publisher for Toronto Raptors On SI. He has been with the website since October 2025. He has appeared on the "Basketball North" podcast and TSN 1050 talking about the Raptors. He graduated from the University of Central Florida with a Bachelor's degree in Broadcast Journalism minoring in Sport Business Management. Brener can be followed on Twitter @JeremyBrener.
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